Concise and scalable synthesis of (±)-phosphonothrixin

[Display omitted] •A concise and scalable method for the synthesis of (±)-phosphonothrixin (total 18% yield in 6 steps).•Phosphonothrixin is an herbicidal antibiotic containing a C–P bond.•A simpler and more responsible method for the synthetic precursor was developed. A concise and scalable method...

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Bibliographic Details
Published in:Results in Chemistry 2021-01, Vol.3, p.100251, Article 100251
Main Authors: Matsushima, Yoshitaka, Nakamura, Koki
Format: Article
Language:English
Subjects:
(±)-Phosphonothrixin
C–P bond
Herbicidal antibiotic
Scalable synthesis
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Summary:[Display omitted] •A concise and scalable method for the synthesis of (±)-phosphonothrixin (total 18% yield in 6 steps).•Phosphonothrixin is an herbicidal antibiotic containing a C–P bond.•A simpler and more responsible method for the synthetic precursor was developed. A concise and scalable method for the synthesis of (±)-phosphonothrixin (1), an herbicidal antibiotic containing a C–P bond, was developed. We developed a simpler and more responsible method for the synthetic precursor, epoxy alcohol 2. The synthetic route is efficient, requiring only six steps to isolate (±)-1 (18%) from the easily obtainable known epoxy alcohol 3 and can be applied to enable gram-scale synthesis.
ISSN:2211-7156
2211-7156
DOI:10.1016/j.rechem.2021.100251